8-(tetrahydro-2H-pyran-4-carbonyl)-N-(4-(trifluoromethoxy)phenyl)-2,8-diazaspiro[4.5]decane-2-carboxamide

ID: ALA2436583

PubChem CID: 72374646

Max Phase: Preclinical

Molecular Formula: C22H28F3N3O4

Molecular Weight: 455.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(OC(F)(F)F)cc1)N1CCC2(CCN(C(=O)C3CCOCC3)CC2)C1

Standard InChI:  InChI=1S/C22H28F3N3O4/c23-22(24,25)32-18-3-1-17(2-4-18)26-20(30)28-12-9-21(15-28)7-10-27(11-8-21)19(29)16-5-13-31-14-6-16/h1-4,16H,5-15H2,(H,26,30)

Standard InChI Key:  QUQUGNOHPPAVRL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   12.5341  -11.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0948   -9.0473    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6548  -11.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3652  -12.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2340  -11.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5301  -12.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5387  -13.3228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5287  -10.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1188  -11.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1023  -10.6928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2585  -13.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3116  -12.6087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1324  -12.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8152   -9.4584    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8200  -11.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6739  -12.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3901   -9.4603    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.8979  -13.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8173  -11.1003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9444  -12.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4556  -13.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6548  -11.0995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9001  -11.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2383  -11.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0792  -11.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1011   -9.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0812  -13.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3489  -11.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7505  -11.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3377  -10.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5187  -10.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1126  -11.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 20  3  1  0
 16 25  1  0
 19 10  1  0
 26 14  1  0
 16  9  1  0
 12 13  1  0
 12 23  1  0
 26  2  1  0
 23 25  1  0
 13  1  1  0
  3  4  1  0
  8 19  2  0
 11 16  1  0
 10 26  1  0
 13  7  2  0
 18 12  1  0
 15  6  2  0
  4 21  1  0
 21 11  1  0
  3 22  2  0
 24  8  1  0
 27 18  1  0
 19 15  1  0
 26 17  1  0
  6  5  1  0
  9  4  1  0
 20  5  1  0
  5 24  2  0
 16 27  1  0
  1 28  1  0
  1 32  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2436583

   8-(oxane-4-carbonyl)-N-[4-(trifluoromethoxy)phenyl]-2,8-diazaspiro[4.5]decane-2-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 455.48

Molecular Weight (Monoisotopic): 455.2032

AlogP: 3.86

#Rotatable Bonds: 3

Polar Surface Area: 71.11

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.75

CX Basic pKa: ┄

CX LogP: 2.80

CX LogD: 2.80

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.75

Np Likeness Score: -1.28

References

1. Kato Y, Fuchi N, Saburi H, Nishimura Y, Watanabe A, Yagi M, Nakadera Y, Higashi E, Yamada M, Aoki T..  (2013)  Discovery of 2,8-diazaspiro[4.5]decane-based trisubstituted urea derivatives as highly potent soluble epoxide hydrolase inhibitors and orally active drug candidates for treating hypertension.,  23  (21): [PMID:24035338] [10.1016/j.bmcl.2013.08.054]

Source

Source(1):

• Scientific Literature